Sodium Hydroxide → 5-Hydroxy-2-methoxypyridine

HRID 1940157Notes

Reaction equation

HRID 1940157 reaction equation
C([O:4][C:5]1[CH:6]=[CH:7][C:8]([O:11][CH3:12])=[N:9][CH:10]=1)(=O)C.[OH-].[Na+]>CO>[OH:4][C:5]1[CH:6]=[CH:7][C:8]([O:11][CH3:12])=[N:9][CH:10]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 224515665-Acetoxy-2-methoxypyridine

Product 1

HCID 116223355-Hydroxy-2-methoxypyridine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of the 5-acetoxy-2-methoxypyridine(600 mg, 3.59 mmol) in MeOH(10 mL) was added 1M aq. NaOH(10 mL, 10 mmol). After stirring at r.t. for 30 min, volatile solvent was removed in vacuo, acidified with HOAc and extracted with CHCl3(3×). The combined CHCl3 extracts were washed with H2O, dried(anhydrous MgSO4) and evaporated to give the title compoud as a brown oil(240 mg, solidified on standing).

Workup

  1. customvolatile solvent was removed in vacuo
  2. extractionextracted with CHCl3(3×)
  3. washThe combined CHCl3 extracts were washed with H2O, dried(anhydrous MgSO4) and
  4. customevaporated
  5. customto give the title compoud as a brown oil(240 mg, solidified on standing)

Sources & evidence

ORD record
ord-4ddfc293fb9c4fb8983b88be218bc28f
Source dataset
uspto-grants-1997_12
Patent number
US05698584

Reaction notes

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